The 21st century classroom is large, diverse, underfunded, and populated by students weaned on digital devices espousing a consumer mentality looking for a good return on investment (ROI) on their education. These students, the so-called "millennials," and the coming Generation Z, who have grown up in the digital age, are more pragmatic than previous generations of students and are less amenable to traditional teaching approaches. While some lament this "crisis" in education, it can be seen as an opportunity. As "digital natives," students are immersed in the newer technologies both as consumers and producers and anticipate remaining plugged in during college and beyond. Harnessing this interest and expertise and effectively integrating these newer technologies into the classroom can help solve this "crisis." Technology enhanced teaching has the potential to transform learning, deepen student engagement, and connect with the more varied and numerous student cohorts. This article explores how effective use of ePortfolios can be aligned with learning goals to create meaningful, engaging, and innovative assignments that transform the classroom from a site of prescriptive learning, where information is unilaterally transmitted, to one of distributed expertise, where knowledge is jointly created, and digitally literate students are equipped to become the life-long, tech-savvy, self-directed learners that this new century demands. But there are no guarantees. This article concludes by acknowledging tensions in the tech-laden classroom, fears that technology is driving pedagogy, poor understanding of key affordances, and misalignment between instructional goals, learning outcomes, and students' understandings.